EP2653606A1 - Faserbehandlungsmittel - Google Patents
Faserbehandlungsmittel Download PDFInfo
- Publication number
- EP2653606A1 EP2653606A1 EP11848125.8A EP11848125A EP2653606A1 EP 2653606 A1 EP2653606 A1 EP 2653606A1 EP 11848125 A EP11848125 A EP 11848125A EP 2653606 A1 EP2653606 A1 EP 2653606A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- treatment agent
- fiber treatment
- formula
- agent according
- fiber
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000835 fiber Substances 0.000 claims abstract description 140
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 107
- -1 ester compound Chemical class 0.000 claims abstract description 93
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 230000001804 emulsifying effect Effects 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 238000009987 spinning Methods 0.000 claims description 10
- 239000012209 synthetic fiber Substances 0.000 claims description 8
- 229920002994 synthetic fiber Polymers 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 4
- 238000007669 thermal treatment Methods 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 238000005096 rolling process Methods 0.000 claims description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 43
- 230000001050 lubricating effect Effects 0.000 description 27
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 21
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 16
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- 150000004665 fatty acids Chemical class 0.000 description 11
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 10
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- 125000002947 alkylene group Chemical group 0.000 description 9
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 8
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- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
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- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 6
- 235000021313 oleic acid Nutrition 0.000 description 6
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 6
- CNVZJPUDSLNTQU-SEYXRHQNSA-N petroselinic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(O)=O CNVZJPUDSLNTQU-SEYXRHQNSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 229960000541 cetyl alcohol Drugs 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 5
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- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229940043348 myristyl alcohol Drugs 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- GJWSUKYXUMVMGX-UHFFFAOYSA-N citronellic acid Chemical compound OC(=O)CC(C)CCC=C(C)C GJWSUKYXUMVMGX-UHFFFAOYSA-N 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 3
- OXEDXHIBHVMDST-UHFFFAOYSA-N 12Z-octadecenoic acid Natural products CCCCCC=CCCCCCCCCCCC(O)=O OXEDXHIBHVMDST-UHFFFAOYSA-N 0.000 description 3
- 235000021357 Behenic acid Nutrition 0.000 description 3
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 3
- 235000021319 Palmitoleic acid Nutrition 0.000 description 3
- CNVZJPUDSLNTQU-UHFFFAOYSA-N Petroselaidic acid Natural products CCCCCCCCCCCC=CCCCCC(O)=O CNVZJPUDSLNTQU-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 229940116226 behenic acid Drugs 0.000 description 3
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000009991 scouring Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 3
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YLZIMEJTDZWVJG-UHFFFAOYSA-N 2-heptylundecanoic acid Chemical compound CCCCCCCCCC(C(O)=O)CCCCCCC YLZIMEJTDZWVJG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- 229930008398 Citronellate Natural products 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
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- 239000003463 adsorbent Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
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- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/02—Processes in which the treating agent is releasably affixed or incorporated into a dispensing means
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/165—Ethers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/34—Esters of monocarboxylic acids
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/165—Ethers
- D06M13/17—Polyoxyalkyleneglycol ethers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
Definitions
- the present invention relates to a fiber treatment agent, and particularly to a fiber treatment agent used in steps of producing and processing fibers with a thermal treatment.
- Fiber manufacturing uses fiber treatment agents such as for imparting smoothness, a focusing property, and an antistatic property according to a purpose to facilitate spinning and/or drawing fibers.
- fiber treatment agents such as for imparting smoothness, a focusing property, and an antistatic property according to a purpose to facilitate spinning and/or drawing fibers.
- lubricating components for fibers including paraffin hydrocarbons such as mineral oils, oleyl oleate, dioleyl adipate, and dioleyl dipropionate.
- JP-B 47-29474 discloses an ester of a bisphenol-alkylene oxide adduct as a lubricating component that has good heat resistance causing little decomposition and small fuming.
- JP-A 06-228866 discloses a technology using an ester compound of 1,2,3,4-butenetetracarboxylic acid as a fiber treatment agent having good heat resistance.
- JP-A 10-245781 discloses a technology using an ester compound having a phenol moiety and an ester of thiodipropionic acid together as a fiber treatment agent having a good heat resistance.
- JP-A 6-010264 discloses a method for sizing carbon fibers, including treating carbon fibers with an aqueous solution containing an ester compound and a nonionic surfactant.
- JP-A 10-251974 discloses a synthetic fiber treatment agent containing two compounds.
- the present invention provides a fiber treatment agent containing an ester compound represented by the formula (1): R 1 -O-((EO) l -(PO) m )-(EO) n -CO-R 2 (1) wherein, R 1 represents a hydrocarbon group having 8 to 24 carbon atoms; R 2 represents an alkyl group, an alkenyl group or a cycloalkyl group, having 7 to 23 carbon atoms; EO represents an ethyleneoxy group; PO represents a propyleneoxy group; 1 and n each represent an average reacted mole number of ethyleneoxy groups, l ranging from 0 to 15 and n ranging from 1 to 20; m represents an average reacted mole number of propyleneoxy groups, ranging from 0.5 to 20; and ((EO) l -(PO) m ) and (EO) n are arranged in block in this order, while (EO) l and (PO) m in ((EO) l -(PO) m ) may
- an aqueous fiber treatment agent is required to have enough stability in an emulsion state for uniform attachment of a lubricating component on fibers.
- an emulsifying component e.g., a surfactant
- a treating agent that can form an emulsion having good stability with a small amount of emulsifying component.
- a fiber treatment agent containing a lubricating component having a high melting point reduces lubricating performance, stability, and/or handling property.
- the present invention provides a fiber treatment agent that contains a lubricating component with a low melting point, is easy to handle, and has all good properties in lubricating performance, heat resistance, and emulsion stability in an aqueous system.
- the present inventors have extensively investigated for solving the above-mentioned problems, and found that an ester compound produced by reacting an alkylene oxide to an alcohol having a specific chain length in a specified manner and reacting with a fatty acid can solve these problems by being used as a lubricating component.
- the present invention thus has been accomplished.
- a fiber treatment agent that contains a lubricating component with a low melting point and is in the liquid state at an ambient temperature, is easy to handle, and has all good properties in lubricating performance, heat resistance, and emulsion stability in an aqueous system.
- the fiber treatment agent is easy to handle at a low temperature, can coat a fiber yarn uniformly, and is easy to remove in scouring and washing before a step of staining or the like, and therefore contributes significantly to facilitating a producing process of fibers.
- the fiber treatment agent of the present invention contains the ester compound represented by the formula (1).
- R 1 represents a hydrocarbon group having 8 to 24 carbon atoms, preferably 10 to 22 carbon atoms, and more preferably 12 to 18 carbon atoms.
- the hydrocarbon group for R 1 include linear and branched alkyl and alkenyl groups and aromatic hydrocarbon groups that may be substituted with a linear or branched alkyl or alkenyl group.
- R 1 preferably represents a linear primary alkyl or alkenyl group, and more preferably a linear primary alkyl group.
- R 1 preferably represents a residual group of a natural higher alcohol such as octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, behenyl alcohol or oleyl alcohol by removing a hydroxy group therefrom.
- a natural higher alcohol such as octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, behenyl alcohol or oleyl alcohol by removing a hydroxy group therefrom.
- R 1 more preferably represents a residual group of an alcohol selected from lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, behenyl alcohol and oleyl alcohol by removing a hydroxy group therefrom, even more preferably represents a residual group of an alcohol selected from lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol and oleyl alcohol by removing a hydroxy group therefrom, and still even more preferably represents a residual group of an alcohol selected from lauryl alcohol, myristyl alcohol, cetyl alcohol and stearyl alcohol by removing a hydroxy group therefrom.
- R 2 represents an alkyl, alkenyl or cycloalkyl group having 7 to 23 carbon atoms, preferably a linear alkyl or alkenyl group having 7 to 23 carbon atoms, more preferably a linear alkyl or alkenyl group having 9 to 21 carbon atoms, and even more preferably a linear alkyl or alkenyl group having 11 to 17 carbon atoms.
- Specific examples of preferred R 2 include residual groups of linear and branched, saturated and unsaturated fatty acids by removing a carboxy group.
- R 2 preferably represents a residual group of a fatty acid selected from octanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, petroselinic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, erucic acid, isopalmitic acid (2-hexyldecanoic acid), 2-heptylundecanoic acid, citronellic acid, and isostearic acid by removing a carboxy group, more preferably represents a residual group of a fatty acid selected from decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid, palmitoleic acid, petroselinic acid, oleic acid, elaidic acid
- l represents the number ranging from 0 to 15, preferably 0 to 5, more preferably 0 to 3, and from the viewpoint of lubricating performance, even more preferably being equal to 0.
- n represent the number ranging from 1 to 20, preferably 2 to 15, more preferably 3 to 12, and from the viewpoint of emulsion stability, even more preferably 4 to 10.
- m represent the number ranging from 0.5 to 20, preferably 0.8 to 15, more preferably 1 to 10, and from the viewpoint of lubricating performance, even more preferably 1.2 to 8.
- (EO) l and (PO) m in ((EO) l -(PO) m ) may be arranged at random or in block.
- (EO) l and (PO) m are preferably arranged in block.
- a key feature is an arrangement of ((EO) l -(PO) m ) and (EO) n in block in this order in the formula (1).
- the arrangement of ((EO) l -(PO) m ) and (EO) n in block in this order makes the ester compound represented by the formula (1) have a low temperature and contribute to improving easiness in handling. Further, the fiber treatment agent containing the ester compound having the arrangement can have all good properties in lubricating performance, heat resistance, and emulsion stability in an aqueous system.
- the ester compound represented by the formula (1) can be obtained, for example, by the following method. Or the ester compound represented by the formula (1) is preferably produced by the following steps (I) to (III):
- R 1 -OH (2) (wherein, R 1 has the same meanings as above) are mixed with a known acid or base catalyst, and if needed, dehydrated at 20 to 140°C under reduced pressure. With the alcohol is reacted (1) propylene oxide alone, (2) ethylene oxide and then propylene oxide, or (3) ethylene oxide and propylene oxide randomly, and then reacted ethylene oxide to give a corresponding alkylene oxide adduct.
- the addition reaction of an alkylene oxide is preferably conducted by introducing the alkylene oxide in a predetermined amount and reacting until a pressure is decreased to a constant level (aging operation) at a temperature of 80 to 180°C.
- the catalyst is neutralized if needed, and removed by filtration with the aid of an alkali adsorbent if additionally needed.
- the resultant alkylene oxide adduct is subjected to esterification or transesterification with one or more fatty acids or fatty acid esters collectively represented by the formula (3): R 2 -COOM (3) (wherein, R 2 has the same meanings as above; and M represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms) by a standard method in the presence of a known catalyst such as a metal, acid or base catalyst if needed to obtain ester compound(s) represented by the formula (1), which may be purified by removing the catalyst with an adsorbent or a steam treatment if needed.
- the fiber treatment agent of the present invention may be in the form of liquid oily agent containing the ester compound represented by the formula (1) [hereinafter, referred to as ester compound (1)], or aqueous emulsion prepared by emulsifying the ester compound (1) in an aqueous medium selected from water and mixtures of water with water-miscible organic solvents (e.g., ethanol and isopropanol).
- ester compound (1) has a tendency of self-emulsifying in an aqueous medium, and thus can reduce other emulsifying agent used together and can prevent separation of other functional agents to provide uniform coating on fibers.
- the fiber treatment agent is preferably used in the form of aqueous emulsion to treat fibers.
- the fiber treatment agent of the present invention preferably contains the ester compound (1) in an amount of 3 to 70% by mass, more preferably 4 to 50% by mass, and even more preferably 5 to 25% by mass.
- the fiber treatment agent of the present invention can preferably further contain one or more components selected from emulsifying component and other functional agents.
- Nonionic surfactants can be used without limitation.
- examples of the nonionic surfactant include hardened castor oil-alkylene oxide adducts, esters of higher alcohols, alkylphenols, and polyhydric alcohols, and alkylene oxide adducts of these esters.
- a known anionic surfactant can be used without limitation.
- anionic surfactant examples include fatty acid salts such as stearates, oleates, and erucates; alkylsulfonate salts, alkylbenzenesulfonate salts, alkylsulfate ester salts, and alkylphosphate ester salts.
- nitrogen-containing compound examples include quaternary alkylammonium salts, alkylhydroxyethylammonium salts, cationic surfactants such as imidazolinium salts, and amphoteric surfactants such as aliphatic alkanolamides, aliphatic amine-ethylene oxide adducts, and alkyl betaines.
- the fiber treatment agent containing the ester compound (1) of the present invention can form a stable emulsion with a less amount of emulsifying component than usual due to a self-emulsifying property of the ester compound (1).
- a content of the emulsifying component in the fiber treatment agent of the present invention can be adjusted within the range of 0 to 50% by mass, and preferably 0.1 to 20% by mass. Even in cases of lowering the content of the emulsifying component to, for example, the range of 0.1 to 5% by mass, particularly to the range of 0.1 to 3% by mass, and more particularly to the range of 0.1 to 2% by mass, the fiber treatment agent of the present invention can form an emulsion having good stability.
- lubricants such as ester oils, such as isostearyl isostearate, isostearyl adipate and trimethylolpropane trilaurate, and mineral oils, such as liquid paraffin
- adhesives such as unmodified, ether-modified, amino-modified, epoxy-modified or glycol-modified silicon resins, polyacrylic esters, polyvinyl alcohols, terminal esterified or etherified adducts of bisphenol A with ethylene oxide
- extreme pressure additives such as alkylamines having 8 to 22 carbon atoms and ethylene oxide adducts thereof; anticorrosives; preservatives, and antioxidants.
- a content of such other functional agent can be adequately determined according to a purpose within the range that does not impair the effects of the present invention.
- Fiber can be coated (lubricated) with the fiber treatment agent of the present invention by a known method, without limitation, such as dipping and spraying.
- fiber is preferably treated in a solution containing the fiber treatment agent at a concentration of 1 to 150 g/L as the ester compound represented by the formula (1).
- fibers are preferably coated with the fiber treatment agent in an amount of 0.02 to 5 parts by mass, more preferably 0.1 to 3 parts by mass, and even more preferably 0.3 to 2 parts by mass, as the ester compound (1), to 100 parts by mass of fibers.
- fibers to which the fiber treatment agent of the present invention is applicable include synthetic fibers such as polyester, polyamide, polyacrylic, polypropylene, polyvinyl alcohol, poly(vinyl chloride), poly(vinylidene chloride) and polyurethane fibers, semisynthetic fibers such as acetate fibers, blended yarns of synthetic or semisynthetic fibers and natural fibers such as cotton, linen, rayon, and wool, and modified synthetic fibers containing inorganic compounds such as titania, zirconia, alumina, silica, zeolite in a dispersed state. These fibers may contain a delustering agent, a fluorescent brightening agent, an antistatic agent, and/or a flame retardant.
- synthetic fibers such as polyester, polyamide, polyacrylic, polypropylene, polyvinyl alcohol, poly(vinyl chloride), poly(vinylidene chloride) and polyurethane fibers
- semisynthetic fibers such as acetate fibers,
- synthetic fibers receive much benefit from the fiber treatment agent of the present invention, because synthetic fibers are generally subjected to a heat treatment at high temperature.
- the fiber treatment agent of the present invention is also applicable to materials such as cotton, linen fabric, and woolen goods treated with conventional lubricants.
- the fiber treatment agent of the present invention can be applied at any timing after a spun yarn is solidified.
- the fiber treatment agent of the present invention is applied onto a yarn at a point before a taking-off roller.
- the fiber treatment agent of the present invention can coat a yarn uniformly when applied, and can be easily washed off in scouring and washing before a staining step or the like.
- the resultant yarn can be used in woven and non-woven fabrics for industrial materials such as clothing fabric, adhesive tape-reinforcing fabric, covering material of cable, fabric for a tent, and tire cord.
- the fiber treatment agent of the present invention can be suitably used as a lubricant for synthetic fiber in high-speed spinning or for tire cord, or may be used as a base oil for lubricating oil used in drawing, direct spin drawing, and spinning fiber to manufacture a fabric, coning oils, and lubricating oil used in entangling fiber to form a fabric.
- the fiber treatment agent of the present invention can be blended with appropriate additive(s) to provide a composition.
- the present invention includes the following aspects:
- Ester compounds (B) to (K) and comparative ester compounds (a) to (g) were prepared in the same reactor, operations, and conditions as in Preparation Example 1, except for reacting an average l moles of ethylene oxide, an average m moles of propylene oxide, and an average n moles of ethylene oxide in this order to starting alcohols shown in Table 1, respectively, under the same conditions as in Preparation Example 1 and then esterifying the resultant with respective fatty acids shown in Table 1. Respective rates of esterification (from the starting fatty acid) and structural features of ester compounds are shown in Table 1.
- Ester compounds shown in Table 1 were evaluated for appearance and heat resistance according to the following methods. These ester compounds shown in Table 1 were used to prepare fiber treatment agents according to the following procedure. Fiber treatment agents were evaluated for lubricating performance and emulsion stability according to the following methods. Results are collectively shown in Table 2.
- An ester compound used as a lubricating component in a fiber treatment agent should be liquid at a treatment temperature to offer a sufficient lubricating performance and be easy to handle at an ambient temperature (20°C).
- An ester compound used as a lubricating component in a fiber treatment agent causes problems such as fuming and a reduced lubricating performance, if it is volatilized or thermally decomposed at a treatment temperature during spinning. Such an ester compound thus should not be volatilized or thermally decomposed at a temperature of spinning (generally about 200°C).
- ester compounds shown in Table 1 were evaluated in term of volatilization and thermal decomposition behavior in a high-temperature region by thermogravimetric analysis.
- ester compounds shown in Table 1 were heated in air flowing at an increasing rate of 10°C/min from an initial temperature 20°C and a temperature (T5) when the ester compound has a reduction of weight corresponding to 5% by weight of the initial weight was determined. Rating was made with the following scale. Results are shown in Table 2.
- Sample yarn (polyester filament yarn: 83 dtex, 36 filaments) was immersed in the fiber treatment agent to be coated with the fiber treatment agent in an amount of 1.5 parts by mass, as the ester compound, to 100 parts by mass of yarn, and dried to give a test yarn.
- the test yarn was tested by a running yarn method with a friction meter (micro tension meter TWD-4, Eiko Sokki Co., Ltd.,), including contacting a running yarn with a metal pin (stainless steel) under conditions of an initial tension of 20 gf, a yarn speed of 500 m/min, and a friction angle of 180°.
- a dynamic friction between the yarn and the metal during the yarn passing through the metal pin was measured five times to calculate an average value. From the average value, a coefficient of dynamic friction was determined. Results are shown in Table 2. The smaller coefficient of dynamic friction refers to the smaller friction of the yarn or the better lubricating performance of the fiber-treatment agent.
- Fiber treatment agents containing ester compounds having a specific structure represented by the formula (1) according to the present invention have all good properties in appearance, heat resistance, lubricating performance and emulsion stability in an aqueous system. Furthermore, the fiber treatment agent of the present invention can be easily removed during scouring and washing, and therefore significantly contribute to facilitating a manufacturing process of fiber.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2010279169A JP5260621B2 (ja) | 2010-12-15 | 2010-12-15 | 繊維用処理剤 |
PCT/JP2011/078739 WO2012081564A1 (ja) | 2010-12-15 | 2011-12-13 | 繊維用処理剤 |
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EP2653606A1 true EP2653606A1 (de) | 2013-10-23 |
EP2653606A4 EP2653606A4 (de) | 2017-10-04 |
EP2653606B1 EP2653606B1 (de) | 2018-09-19 |
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EP11848125.8A Active EP2653606B1 (de) | 2010-12-15 | 2011-12-13 | Faserbehandlungsmittel |
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EP (1) | EP2653606B1 (de) |
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CN (1) | CN103210138B (de) |
ES (1) | ES2692870T3 (de) |
WO (1) | WO2012081564A1 (de) |
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JP6434904B2 (ja) * | 2013-03-13 | 2018-12-05 | 松本油脂製薬株式会社 | 合成繊維フィラメント用処理剤、合成繊維フィラメント及び基布 |
WO2015008591A1 (ja) * | 2013-07-19 | 2015-01-22 | 松本油脂製薬株式会社 | 合成繊維用処理剤およびその用途 |
CN103437166B (zh) * | 2013-09-02 | 2015-04-29 | 苏州市轩德纺织科技有限公司 | 一种浆纱用油剂 |
CN104099781B (zh) * | 2014-07-11 | 2016-07-06 | 上海多纶化工有限公司 | 无磷纺织精练剂 |
CN108368671B (zh) * | 2016-03-04 | 2019-06-28 | 松本油脂制药株式会社 | 合成纤维用处理剂及其用途 |
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US4110227A (en) * | 1977-09-19 | 1978-08-29 | Basf Wyandotte Corporation | Oxidation stable polyoxyalkylene fiber lubricants |
US4830769A (en) * | 1987-02-06 | 1989-05-16 | Gaf Corporation | Propoxylated guerbet alcohols and esters thereof |
US5270113A (en) * | 1989-09-05 | 1993-12-14 | E. I. Du Pont De Nemours And Company | Highly processable aromatic polyamide fibers, their production and use |
DE4106682C2 (de) * | 1991-03-02 | 1995-08-10 | Du Pont | Aromatische Hochleistungs-Polyamid-Fasern, ihre Herstellung und Verwendung |
JP2590576B2 (ja) * | 1990-01-17 | 1997-03-12 | 東レ株式会社 | 高速紡糸用合成繊維処理油剤 |
US5240743A (en) * | 1992-02-28 | 1993-08-31 | Henkel Corporation | Fiber finishing methods |
JP3169468B2 (ja) | 1992-03-27 | 2001-05-28 | 竹本油脂株式会社 | 炭素繊維のサイジング方法 |
JPH06228866A (ja) | 1993-02-02 | 1994-08-16 | New Japan Chem Co Ltd | 繊維用油剤 |
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JPH10245781A (ja) | 1997-02-28 | 1998-09-14 | Sanyo Chem Ind Ltd | 合成繊維用処理剤 |
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2010
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- 2011-12-13 ES ES11848125.8T patent/ES2692870T3/es active Active
- 2011-12-13 US US13/991,830 patent/US20130260028A1/en not_active Abandoned
- 2011-12-13 WO PCT/JP2011/078739 patent/WO2012081564A1/ja active Application Filing
Non-Patent Citations (1)
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WO2012081564A1 (ja) | 2012-06-21 |
JP2012127020A (ja) | 2012-07-05 |
JP5260621B2 (ja) | 2013-08-14 |
EP2653606A4 (de) | 2017-10-04 |
EP2653606B1 (de) | 2018-09-19 |
CN103210138A (zh) | 2013-07-17 |
CN103210138B (zh) | 2014-09-17 |
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